Pussy Training Stories

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First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

The Set Up Pt. 02

by undermythumb10 on Sep 15, 2017
Fetish

This is the continued story of my life as a sissy and is a continuation from part 1 The Set Up. ***** As I mentioned I am sat tied to a chair with my stepdaughters panties placed so the crutch is over my nose, it's a long story which started when I met and married my wife now Mistress some six months ago. I am now a total submissive sissy cum slut for my...

Training Tina, Days 03

by rivertown_rat on Sep 13, 2017
BDSM

Being a Pasty Chef Sherry was up and away early. I had told Tina to be ready by 8:00. I was technically on vacation so I saw no reason to get going too early. When I heard the shower running downstairs I knew Tina was up. I snoozed for another 30 minutes and then I got up and hit the shower myself. After I got dressed and went out to the living room I found...

The Ten Thousand Dollar Decision Ch. 02

by spankedhusband on Sep 13, 2017
BDSM

I'd slept fitfully after Gloria's surprising – I guess that shocking would more accurately describe it – pronouncements the night before. To say that my feelings were ambiguous would be an understatement. Desire and arousal on one hand fought with abject fear on another. Excitement at the thought of at last realizing my innermost desires coupled with the re...

Awakening of Fannie Ch. 13

by STEVEN VANE on Sep 18, 2017
BDSM

(The following story relates to the slut/slave training of a former prim and proper housewife sent to be trained by a professional Master by her husband. She will not be the same woman when he gets her back home!) Day 3 The past two days seemed like a nightmare! Fannie has been beaten, deprived of sleep and forced to lick shit from another woman's ass!...

Lucy's Training Ch. 01

by JamesBlonde on Oct 13, 2017
BDSM

Training Evening It's a warm November evening in LA, after we've moved there, and I tell you that I have a surprise for you. In the afternoon, we've spent time in our pool, me babying you and then lying around naked in the warmth. Before we moved there I insisted that you got your breasts and butt enlarged so that you would be better proportioned than all t...

Pony Wants To Please The Mistress

by marla_gillis on Sep 17, 2017
Fetish

JJ the pony wants to please the Mistress. He is new to being a pony, so he is trying extra hard to be good. JJ has a strong back, a tight ass, and a beautiful cock. He has sweet eyes and a handsome face. JJ makes a great pony. Ponies are generally considered intelligent and friendly, though sometimes they also are described as stubborn or cunning. Mistress...

Estate Debt Slaves

by jjskylark on Sep 25, 2017
BDSM

The two new slave girls took turns mounting the Estate master's cock as he lay on a blanket in his newly constructed pleasure garden. The rules for each young woman were simple... squat over her master's rigid staff and lower herself ever-slowly onto his waiting erection while the other girl held it up for her until the slave's pussy lips encompassed no more...

A Yank in Britain

by CharlieL on Sep 14, 2017
Erotic Couplings

I had been in the US Air Force for a total of 4 years and had just received my bars for my promotion to Captain. Really a pretty good promotion record since I had enlisted as a 2nd Lt, got promoted to 1st. Lt. a year later and here I was a full- fledged Captain three years after that. After my flight training down in Texas they transferred me up to Kansas fo...

Basic Training Adventure

by LuckyMartian on Feb 12, 2019
Exhibitionist & Voyeur

Basic training in the military is a bitch until you get used to it. After that it gets to be routine. Routine if you think being in an open bay barracks with 20 other horny guys is desirable. However, bless the military they don't give you much time to think about sex and you are too tired in the evening to do anything about it usually. That could be a good...